1-Naphthaldehyde → HCID 12192538, compound

HRID 2213978Notes

Reaction equation

HRID 2213978 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:24]=CC=C[CH:20]=1.[PH4+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CCCCCC.C1(C)C=CC=CC=1>[CH2:19]([CH:24]=[CH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:20]

Participants

7

Reactant 4

HCID 61951-NaphthaldehydeHCID 11430Potassium CarbonateHCID 13097Triphenylphosphine OxideHCID 5460504Phosphonium

Product 1

HCID 12192538HCID 12192538, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 21889329Toluene hexaneSolvent

Procedure

1-(ethyl)-2-(naphthyl)ethylene (IXd) was prepared from 1.00 g (2.7 mmol) of (ethyl)triphenylphosphonium bromide (Vd), 0.42 g (2.7 mmol) of naphthaldehyde and 0.79 g (5.5 mmol) of anhydrous K2CO3 by ball-milling for 26 hours. The formed powder was analyzed by the solid state 31P MAS NMR spectroscopy. The solid state 31P MAS NMR spectrum of the ball-milled powder contained two signals: a major signal corresponding to triphenylphosphine oxide at δ31P=25 ppm and a minor signal corresponding to the starting phosphonium salt at δ13P=30 ppm, the estimated ratio ˜8:1. The powder (2.0 g) was loaded on the top of a silica-gel filled chromatographic column, and the mixture of (E)- and (Z)-isomers was isolated by eluation with a hexane-toluene mixture (E:Z ratio ca. 1:1 by 1H NMR in CDCl3) in the 63% yield, (0.26 g). Triphenylphosphine oxide was further obtained from the same column in 80% yield (0.61 g) using a hexane-acetone mixture as an eluant. Assignment of the signals in the 13C and 1H NMR spectra of the reaction products was performed according to the literature (see, e.g., Kulasegarm, et al., J. Org. Chem. 62, 6547 (1997); Kulasegarm et al., Tetrahedron 54, 1361(1998)).

Workup

  1. additionfilled chromatographic column

Sources & evidence

ORD record
ord-30f0940439864e44ab462e825e82d963
Source dataset
uspto-grants-2006_09
Patent number
US07105714B2

Reaction notes

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